ES2537407T3 - Cure accelerators for anaerobic curable compositions - Google Patents
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/765—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
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- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/3293—Hydroxyamines containing heterocyclic groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
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- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
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Abstract
Un producto de reacción preparado a partir de reactivos que comprende: (a) un compuesto abarcado por la estructura A donde X es alquilo C1-20, alquenilo C2-20 o alquilarilo C7-20, cualquiera de los cuales puede estar interrumpido por uno o más heteroátomos, y que están funcionalizados con al menos uno y preferentemente al menos dos grupos seleccionados de -OH, -NH2 o -SH y z es 1-3 y (b) al menos un material isocianato funcional.A reaction product prepared from reagents comprising: (a) a compound encompassed by structure A where X is C1-20 alkyl, C2-20 alkenyl or C7-20 alkylaryl, any of which may be interrupted by one or more heteroatoms, and which are functionalized with at least one and preferably at least two groups selected from -OH, -NH2 or -SH and z is 1-3 and (b) at least one functional isocyanate material.
Description
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Los materiales isocianato funcionales pueden comprender (met)acrilatos isocianato funcionales. The isocyanate functional materials may comprise (meth) functional isocyanate acrylates.
El producto de reacción del compuesto o los compuestos de estructura A con el material funcional de isocianato pueden comprender de aproximadamente un 5 a aproximadamente un 99 por ciento en peso del peso total de los reactivos usados para preparar el producto de reacción, o de aproximadamente un 50 a aproximadamente un 95 por ciento en peso o aproximadamente un 85 por ciento en peso de los reactivos. El material funcional de isocianato puede comprender de aproximadamente un 1 a aproximadamente un 30 por ciento en peso del peso total de los reactivos usados para preparar el producto de reacción, o de aproximadamente un 10 a aproximadamente un 30 por ciento en peso, o aproximadamente un 25 por ciento en peso de los reactivos. The reaction product of the compound or compounds of structure A with the isocyanate functional material may comprise from about 5 to about 99 percent by weight of the total weight of the reagents used to prepare the reaction product, or from about a 50 to about 95 percent by weight or about 85 percent by weight of the reagents. The isocyanate functional material may comprise from about 1 to about 30 percent by weight of the total weight of the reagents used to prepare the reaction product, or from about 10 to about 30 percent by weight, or about a 25 percent by weight of reagents.
El producto de reacción de estructura A y el material isocianato funcional pueden tener funcionalidad isocianato residual que puede hacerse reaccionar adicionalmente con materiales hidroxi, tio y/o amino funcionales, tales como (met)acrilatos hidroxi, tio y/o amino funcionales y éteres de vinilo hidroxi funcionales. The reaction product of structure A and the functional isocyanate material can have residual isocyanate functionality which can be further reacted with functional hydroxy, thio and / or amino materials, such as (meth) hydroxy, thio and / or amino functional acrylates and ethers of functional hydroxy vinyl.
El producto o productos de reacción hidroxi funcionales del compuesto o los compuestos de estructura A y los materiales isocianato funcionales forman enlaces uretano. El producto de reacción hidroxi funcional así formado se hace reaccionar con el compuesto o compuestos de poliisocianato para formar un prepolímero de uretano isocianato funcional y posteriormente se hace reaccionar con un monómero de (met)acrilato reactivo, tal como un (met)acrilato hidroxi funcional, para producir un polímero o una resina basados en di(met)acrilato que incluye un resto acelerante funcional. The functional hydroxy reaction product or products of the compound or compounds of structure A and the isocyanate functional materials form urethane bonds. The functional hydroxy reaction product thus formed is reacted with the polyisocyanate compound or compounds to form a functional isocyanate urethane prepolymer and subsequently reacted with a reactive (meth) acrylate monomer, such as a functional hydroxy (meth) acrylate , to produce a polymer or resin based on di (meth) acrylate which includes a functional accelerating moiety.
El producto de reacción amino funcional del compuesto o compuestos de estructura A se hace reaccionar después con materiales isocianato funcionales para formar enlaces urea. El producto de reacción amino funcional de estructura A así formado se hace reaccionar después con un compuesto o compuestos de poliisocianato que forma un prepolímero de urea isocianato funcional y se hace reaccionar posteriormente con un monómero de (met)acrilato reactivo, tal como un (met)acrilato hidroxi funcional, para producir un polímero o una resina basados en di(met)acrilato que incluye un resto acelerante funcional. The amino functional reaction product of the compound or compounds of structure A is then reacted with functional isocyanate materials to form urea bonds. The amino functional reaction product of structure A thus formed is then reacted with a polyisocyanate compound or compounds that forms a functional urea isocyanate prepolymer and subsequently reacted with a reactive (meth) acrylate monomer, such as a (met ) functional hydroxy acrylate, to produce a polymer or resin based on di (meth) acrylate which includes a functional accelerating moiety.
El producto de reacción tiol funcional del compuesto o compuestos de estructura A y los materiales isocianato funcionales forman enlaces carbamotioato. El producto de reacción tiol funcional así formado se hace reaccionar después con un compuesto o compuestos de poliisocianato para formar un prepolímero de carbamotioato isocianato funcional y posteriormente se hace reaccionar con un monómero de (met)acrilato reactivo, tal como un (met)acrilato hidroxi funcional, para producir un polímero o una resina basados en di(met)acrilato que incluye un resto acelerante funcional. The functional thiol reaction product of the compound or compounds of structure A and the isocyanate functional materials form carbamothioate bonds. The functional thiol reaction product thus formed is then reacted with a polyisocyanate compound or compounds to form a functional isocyanate carbamothioate prepolymer and subsequently reacted with a reactive (meth) acrylate monomer, such as a hydroxy (meth) acrylate functional, to produce a polymer or resin based on di (meth) acrylate that includes a functional accelerating moiety.
La frase "(met)acrilato hidroxi-funcional" significa cualquier compuesto acrilato o metacrilato hidroxi-sustituido que sería adecuado para hacer y usar un material de uretano tapado, los ejemplos de los adecuados incluyen acrilato de hidroxietilo, acrilato de hidroxipropilo, acrilato de hidroxibutilo, metacrilato de hidroxietlo ("HEMA"), metacrilato de hidroxipropilo ("HPMA"), metacrilato de hidroxibutilo y mezclas de los mismos. Otros ejemplos de los (met)acrilatos hidroxi funcionales adecuados incluyen acrilato de 2-hidroxietilo, acrilato de 2-hidroxipropilo, metacrilato de 2hidroximetilo ("HEMA"), tiracrilato de pentaeritritol ("PETA") y acrilato de 4-hidroxibutilo. The phrase "(meth) hydroxy-functional acrylate" means any hydroxy-substituted acrylate or methacrylate compound that would be suitable for making and using a capped urethane material, examples of suitable include hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate , hydroxyethyl methacrylate ("HEMA"), hydroxypropyl methacrylate ("HPMA"), hydroxybutyl methacrylate and mixtures thereof. Other examples of suitable functional hydroxy (meth) acrylates include 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxymethyl methacrylate ("HEMA"), pentaerythritol tyrosacrylate ("PETA") and 4-hydroxybutyl acrylate.
La frase "éter de vinilo hidroxi funcional" significa cualquier éter de vinilo hidroxi sustituido que sería adecuado para hacer y usar un oligómero de uretano tapado, los ejemplos de los adecuados incluyen éteres de vinilo de hidroxietilo, éteres de vinilo de hidroxipropilo, éteres de vinilo de hidroxibutilo y mezclas de los mismos, tales como éter de monovinilo de etilenglicol y éter de monovinilo de dimetanol de ciclohexano. The phrase "functional hydroxy vinyl ether" means any substituted hydroxy vinyl ether that would be suitable for making and using a capped urethane oligomer, examples of suitable include hydroxyethyl vinyl ethers, hydroxypropyl vinyl ethers, vinyl ethers of hydroxybutyl and mixtures thereof, such as ethylene glycol monovinyl ether and cyclohexane dimethane monovinyl ether.
El (met)acrilato hidroxi-funcional puede tener un número medio de peso molecular de aproximadamente 80 a aproximadamente 1.000 gramos/mol, o de aproximadamente 100 a aproximadamente 800 gramos/mol o de aproximadamente 110 a aproximadamente 600 gramos/mol. The hydroxy-functional (meth) acrylate can have an average molecular weight number of about 80 to about 1,000 grams / mole, or about 100 to about 800 grams / mole or about 110 to about 600 grams / mole.
El (met)acrilato hidroxi-funcional puede comprender de aproximadamente un 1 a aproximadamente un 30 por ciento en peso de los reactivos usados para preparar el uretano, o de aproximadamente un 2 a aproximadamente un 15 por ciento en peso de los reactivos o de aproximadamente un 3 a aproximadamente un 12 por ciento en peso de los reactivos. The hydroxy-functional (meth) acrylate may comprise from about 1 to about 30 percent by weight of the reagents used to prepare the urethane, or from about 2 to about 15 percent by weight of the reagents or about 3 to about 12 percent by weight of the reagents.
En algunas realizaciones, el producto de reacción se prepara a partir de un reactivo adicional seleccionado del compuesto o compuestos hidroxi-, amino- y/o tio-funcionales. En estas realizaciones, el producto de reacción puede tener un número medio de peso molecular de aproximadamente 100 a aproximadamente 20.000 gramos/mol, o de aproximadamente 500 a aproximadamente 20.000 gramos/mol, o de aproximadamente 500 a aproximadamente In some embodiments, the reaction product is prepared from an additional reagent selected from the hydroxy-, amino- and / or thio-functional compound or compounds. In these embodiments, the reaction product may have an average molecular weight number of about 100 to about 20,000 grams / mol, or about 500 to about 20,000 grams / mole, or about 500 to about
5.000 gramos/mol o aproximadamente 3.000 gramos/mol. 5,000 grams / mol or approximately 3,000 grams / mol.
Los compuestos hidroxi-, amino- y/o tio-funcionales adecuados para usar en la preparación de los productos monoméricos anteriores se ejemplifican por tales materiales como acrilato de hidroxietilo, metacrilato de hidroxietilo, metacrilato de aminoetilo, metacrilato de 3-hidroxipropilo, metacrilato de aminopropilo, acrilato de hidroxihexilo, metacrilato de t-butilaminoetilo, metacrilato de hidroxioctilo y similares. The hydroxy-, amino- and / or thio-functional compounds suitable for use in the preparation of the above monomeric products are exemplified by such materials as hydroxyethyl acrylate, hydroxyethyl methacrylate, aminoethyl methacrylate, 3-hydroxypropyl methacrylate, aminopropyl, hydroxyhexyl acrylate, t-butylaminoethyl methacrylate, hydroxyoctyl methacrylate and the like.
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en cualquier valor. Como problema técnico, sin embargo, un límite superior general es aproximadamente 50 átomos de carbono, preferentemente 30 y más preferentemente aproximadamente 20. In any value. As a technical problem, however, a general upper limit is about 50 carbon atoms, preferably 30 and more preferably about 20.
Por ejemplo, X puede ser un radical orgánico de la fórmula: For example, X may be an organic radical of the formula:
en la que cada uno de Y1 e Y2 es un radical orgánico, preferentemente un grupo hidrocarburo, que contiene al menos 2 átomos de carbono, y preferentemente de 2 a aproximadamente 10 átomos de carbono, y Z es un radical wherein each of Y1 and Y2 is an organic radical, preferably a hydrocarbon group, containing at least 2 carbon atoms, and preferably 2 to about 10 carbon atoms, and Z is a radical
10 orgánico, preferentemente un grupo hidrocarburo, que contiene al menos 1 átomo de carbono, y preferentemente de 2 a aproximadamente 10 átomos de carbono. 10, preferably a hydrocarbon group, containing at least 1 carbon atom, and preferably from 2 to about 10 carbon atoms.
Otras clases de monómeros útiles son los productos de reacción de di- o tri-alquilolaminas (por ejemplo, etanolaminas o propanolaminas) con ácidos acrílicos, tales como los que se desvelan en la Patente francesa Nº Other classes of useful monomers are the reaction products of di- or tri-alkyllamines (for example, ethanolamines or propanolamines) with acrylic acids, such as those disclosed in French Patent No.
15 1.581.361. 15 1,581,361.
Los ejemplos de los oligómeros de éster acrílico útiles incluyen aquellos que tienen la siguiente fórmula general: Examples of useful acrylic ester oligomers include those that have the following general formula:
30 m es un entero igual a al menos 1, por ejemplo, de 1 a aproximadamente 15 o mayor, y preferentemente de 1 a aproximadamente 8; n es un entero igual a al menos 1, por ejemplo, 1 a aproximadamente 40 o más, y preferentemente entre aproximadamente 2 y aproximadamente 10; y p es 0 o 1. 30 m is an integer equal to at least 1, for example, from 1 to about 15 or greater, and preferably from 1 to about 8; n is an integer equal to at least 1, for example, 1 to about 40 or more, and preferably between about 2 and about 10; and p is 0 or 1.
35 Los ejemplos típicos de oligómeros de éster acrílico que corresponden a la fórmula general anterior incluyen dimetacrilato de di-, tri-y tetraetilenglicol; di(pentametilenglicol)dimetacrilato; diacrilato de tetraetilenglicol; di(cloroacrilato) de tetraetilenglicol; diacrilato de diglicerol; tetrametacrilato de diglicerol; dimetacrilato de butilenglicol; diacrilato de pentilglicol; y triacrilato de trimetilolpropano. Typical examples of acrylic ester oligomers corresponding to the above general formula include di-, tri- and tetraethylene glycol dimethacrylate; di (pentamethylene glycol) dimethacrylate; tetraethylene glycol diacrylate; tetraethylene glycol di (chloroacrylate); diglycerol diacrylate; diglycerol tetramethacrylate; butylene glycol dimethacrylate; pentyl glycol diacrylate; and trimethylolpropane triacrylate.
40 Mientras que los di- y otros ésteres de poliacrilato, y particularmente los ésteres de poliacrilato descritos en los párrafos anteriores, pueden ser deseables, los ésteres de acrilato monofuncionales (ésteres que contienen un grupo acrilato) también pueden usarse. Cuando se trata con ésteres de acrilato monofuncionales, se prefiere altamente usar un éster que tenga un resto alcohólico relativamente polar. Tales materiales son menos volátiles que los ésteres de alquilo de bajo peso molecular y, más importante, el grupo polar tiende a proporcionar atracción While the di- and other polyacrylate esters, and particularly the polyacrylate esters described in the preceding paragraphs, may be desirable, monofunctional acrylate esters (esters containing an acrylate group) can also be used. When treated with monofunctional acrylate esters, it is highly preferred to use an ester having a relatively polar alcoholic moiety. Such materials are less volatile than low molecular weight alkyl esters and, more importantly, the polar group tends to provide attraction
45 intermolecular durante y después de una cura, produciendo de esta manera más propiedades de cura deseables, así como un sellante o un adhesivo de mayor duración. Más preferentemente, el grupo polar se selecciona del grupo que consiste en un hidrógeno lábil, un anillo heterocíclico, grupos hidroxi, amino, ciano y halo polares. Los ejemplos típicos de compuestos dentro de esta categoría son ciclohexilmetacrilato, metacrilato de tetrahidrofurfurilo, acrilato de hidroxietilo, metacrilato de hidroxipropilo, metacrilato de t-butilaminoetilo, cianoetilacrilato y metacrilato de 45 intermolecular during and after a cure, thereby producing more desirable cure properties, as well as a sealant or a longer lasting adhesive. More preferably, the polar group is selected from the group consisting of a labile hydrogen, a heterocyclic ring, hydroxy, amino, cyano and halo halo groups. Typical examples of compounds within this category are cyclohexylmethacrylate, tetrahydrofurfuryl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate, t-butylaminoethyl methacrylate, cyanoethyl acrylate and methacrylate.
50 cloroetilo. 50 chloroethyl
Otra clase útil de monómeros se prepara por la reacción de un éster de acrilato de alquilo o arilo monofuncionalmente sustituido que contiene un átomo de hidrógeno activo en el sustituyente funcional. Este material monofuncional acrilato-terminado se hace reaccionar con un poliisocianato orgánico en proporciones 55 adecuadas para convertir todos los grupos isocianato en grupos uretano o ureido. Los ésteres de acrilato de alquilo y Another useful class of monomers is prepared by the reaction of a monofunctionally substituted alkyl or aryl acrylate ester containing an active hydrogen atom in the functional substituent. This acrylate-terminated monofunctional material is reacted with an organic polyisocyanate in suitable proportions to convert all isocyanate groups into urethane or ureido groups. The alkyl acrylate esters and
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17465209P | 2009-05-01 | 2009-05-01 | |
| US174652P | 2009-05-01 | ||
| PCT/US2010/032869 WO2010127053A2 (en) | 2009-05-01 | 2010-04-29 | Cure accelerators for anaerobic curable compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2537407T3 true ES2537407T3 (en) | 2015-06-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| ES10770297.9T Active ES2537407T3 (en) | 2009-05-01 | 2010-04-29 | Cure accelerators for anaerobic curable compositions |
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|---|---|
| US (1) | US8362112B2 (en) |
| EP (1) | EP2424931B1 (en) |
| JP (1) | JP5620978B2 (en) |
| KR (1) | KR101659111B1 (en) |
| CN (1) | CN102549058B (en) |
| ES (1) | ES2537407T3 (en) |
| WO (1) | WO2010127053A2 (en) |
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|---|---|---|---|---|
| CN104053737B (en) * | 2011-08-03 | 2016-09-07 | 汉高知识产权控股有限责任公司 | The construction adhesive of conduction |
| US9365750B2 (en) * | 2012-06-27 | 2016-06-14 | Henkel IP & Holding GmbH | Accelerators for curable compositions |
| US8986847B2 (en) * | 2012-06-27 | 2015-03-24 | Henkel IP & Holding GmbH | Accelerator/oxidant/proton source combinations for two part curable compositions |
| WO2016018553A1 (en) | 2014-07-30 | 2016-02-04 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
| CN106715559B (en) * | 2014-10-01 | 2020-02-28 | 汉高知识产权控股有限责任公司 | Curing accelerators for anaerobic curable compositions |
| US9657213B2 (en) * | 2014-10-20 | 2017-05-23 | Kraton Polymers U.S. Llc | Curable, resealable, swellable, reactive sealant composition for zonal isolation and well integrity |
| CN107148411B (en) | 2014-10-22 | 2020-06-19 | 汉高知识产权控股有限责任公司 | Phenylhydrazine/anhydride adducts and anaerobically curable compositions using phenylhydrazine/anhydride adducts |
| GB2531717B (en) * | 2014-10-24 | 2016-10-05 | Henkel IP & Holding GmbH | Anaerobic curable compositions |
| CN104934550A (en) * | 2015-05-07 | 2015-09-23 | 京东方科技集团股份有限公司 | OLED device packaging structure, packaging method and electronic device |
| KR102351378B1 (en) | 2015-07-20 | 2022-01-20 | 삼성디스플레이 주식회사 | Adhesive composition and display device |
| CN108368220B (en) * | 2015-10-16 | 2021-05-25 | 汉高知识产权控股有限责任公司 | Reactive resins made from renewable sources |
| CN108473644A (en) * | 2015-12-08 | 2018-08-31 | 汉高知识产权控股有限责任公司 | Functionalized acceleration resin derived from recyclable materials |
| TWI738730B (en) * | 2016-03-29 | 2021-09-11 | 德商漢高智慧財產控股公司 | Two part curable compositions |
| GB2567242B (en) * | 2017-10-09 | 2021-08-11 | Henkel IP & Holding GmbH | Anaerobically curable compositions comprising 1, 2, 3, 4-tetrahydro benzo(h)quinolin-3-ol or derivatives thereof |
| MX2020006412A (en) * | 2017-12-19 | 2020-08-27 | Henkel IP & Holding GmbH | Impregnation sealant for electronic components. |
| EP4061864B1 (en) * | 2019-11-18 | 2023-10-18 | Henkel AG & Co. KGaA | One component (1k) anaerobic curable composition |
| WO2022037909A1 (en) | 2020-08-18 | 2022-02-24 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
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| US4512990A (en) * | 1982-02-18 | 1985-04-23 | Syntex (U.S.A.), Inc. | Benzthiazine analogs as antiinflammatory agents |
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| IE20000440A1 (en) * | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid one- or two-part compositions |
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| US6897277B1 (en) | 2003-12-22 | 2005-05-24 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| US7411025B1 (en) * | 2003-12-22 | 2008-08-12 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| US20090012202A1 (en) * | 2007-07-03 | 2009-01-08 | Henkel Corporation | Acrylated Urethanes, Processes for Making the Same and Curable Compositions Including the Same |
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2010
- 2010-04-29 WO PCT/US2010/032869 patent/WO2010127053A2/en active Application Filing
- 2010-04-29 CN CN201080029817.1A patent/CN102549058B/en not_active Expired - Fee Related
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- 2010-04-29 JP JP2012508668A patent/JP5620978B2/en not_active Expired - Fee Related
- 2010-04-29 EP EP10770297.9A patent/EP2424931B1/en active Active
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2011
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| EP2424931A2 (en) | 2012-03-07 |
| CN102549058B (en) | 2014-03-12 |
| WO2010127053A3 (en) | 2011-03-03 |
| KR20120014915A (en) | 2012-02-20 |
| JP5620978B2 (en) | 2014-11-05 |
| JP2012525481A (en) | 2012-10-22 |
| KR101659111B1 (en) | 2016-09-22 |
| EP2424931B1 (en) | 2015-03-04 |
| EP2424931A4 (en) | 2014-04-30 |
| US8362112B2 (en) | 2013-01-29 |
| CN102549058A (en) | 2012-07-04 |
| US20120129994A1 (en) | 2012-05-24 |
| WO2010127053A2 (en) | 2010-11-04 |
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